Florida Trippin'... Part Four

Warning and disclaimer: In the past I have, for the most part, refrained from talking about Linda and my sexual escapades in detail, instead just glossing over the ‘dirty parts’ in general terms. Because of what has taken place over the last week I do not feel that I can continue that way or, by omitting those details, that I would be doing justice to this adventure or to my faithful masses. So if you are offended by blogs that delve into the sexual details, then I would suggest that you bypass my blog for the next several days.

“That would be your date, Beverly,” Darryl casually remarked as he set down his wine glass and walked to the door. I looked to Linda to gauge her reaction, only to find her smiling back at me. Of course she knew all about this. She and Darryl had been cooking this up for weeks. How could I not see this coming?

Before I could say anything to her, Darryl opened the door and stood back to let the stranger in. In stepped a man in a black suit, standing around 6’1”, brown wavy hair with just a touch of grey in the temples, and, I had to admit, quite nice looking… for a man!

While I was looking at the stranger, Linda and slid over beside me and whispered in my ear, “Not bad. Just go along with things this evening and let yourself enjoy the adventure. If you just relax, I know you will have a good time.” Then she stepped over beside Darryl as he introduced his guest to her.

“This lovely lady is my friend, Linda,” Darryl gleamed. “Linda, this is my old friend, and the owner of this condo, Roger.” As Linda held out her hand, Roger took it and then leaned over and gave Linda a kiss on the cheek. I saw the smile dance on her face as he did.

Then Darryl was looking at me and stating, “And this is your date for this evening. Beverly come over here and meet Roger. He won’t bite, at least not at first.” The three of them laughed at the little joke as I somehow managed to find my legs and slowly stepped over to them. Roger repeat the same welcoming that he had given Linda; warmly taking my hand and then bending to place a kiss on my cheek. I know I was blushing as this transpired, however, it was an accepting blush as the offered kiss felt kind of nice.

Fortunately, I was rescued from the moment by Darryl asking (telling) me to get a glass for Roger as he uncorked another bottle of wine. I paused in the kitchen to catch my breath, my thoughts rushing over all that had just taken place. I had a date for the night! With a MAN!!!

Finally, I knew I couldn’t stall any longer and I returned with glass in hand to the living room. The three of them were seated, Linda next to Darryl on the sofa, and Roger on the loveseat. He looked up expectantly as I handed him the glass, and I knew that I was suppose to join him. As I sat, Darryl got up and brought my glass and the wine to us and poured us a glass. Then, rejoining Linda, he offered a toast.

“Here’s to the end of 2008, and bringing in the new year with dear friends, old and new.”

Roger clicked his glass against mine, then took a drink, his eyes never leaving mine. “Oh, this is going to be a long night,” I thought. Small talk filled the next hour as Linda told Roger how much we enjoyed his condo and how nice it was. Roger talked a little about his real estate holding, which were quite impressive. He and Darryl exchanged a few stories about their mutual past.

Darryl looked at the clock on the mantle and stated that we had best be on our way to dinner. He had made reservations at The Colonnade, a wonderful seafood restaurant he added. Since the night air was chilly, Linda and I went to the bedroom to get our evening wraps.

As we stepped into the room, I immediately exclaimed, “Did you know about this? What’s the big idea? Does Roger know about me, about us?” The words rushed out as I nervously paced the room.

Linda just laughed and replied, “Yes, Roger knows about you being a man who loves to dress up, and he knows we are married. He also knows that I am with Darryl while we are here and that you and I are temporarily unmarried. So you don’t have to worry about him ‘finding out’ anything about you. He already knows, and Darryl tells me that he really likes the idea as well. Darryl says he is not sure, but thinks that Roger is either gay, or at least bi because it has been awhile since Roger has talked about going out with any women. So, see, you have nothing to worry about.”

“Nothing to worry about? You guys have set me up to be a date of some guy who is probably gay, and I have nothing to worry about? I think that gives me a lot to worry about,” I exclaimed.

“Well, it’s not like you have to jump into bed with him… not unless you want to,” Linda teased. Before I could reply, she picked up my wrap and handed it to me. Grabbing hers, she pushed me out the door. I started to put my wrap on as we walked back to the living room (lion’s den?). Linda stopped me, whispering, “Let Roger help you with that.”

As I watched, she walked up to Darryl and handed him her wrap, which he slipped over her shoulders. Suddenly, my wrap was being pulled out of my hands and I turned to see Roger placing it on my shoulders. I quietly uttered “thank you” as he smiled warmly at me. Then we grabbed our purses and were escorted out the door.

The drive proved to be a welcomed relief as I sat in the back seat with Roger (it’s nice to have someone open doors for you!). It provided us with the time and opportunity to chat and for me to relax… a little. Turns out Roger was a very nice guy who seemed to take a genuine interest in me. We found ourselves having our own private conversation and the two in the front seats left us alone. By the time we reached the restaurant, we were starting to act like a dating couple and I allowed him to hold my hand as we walked in. I caught Linda’s quick glance and serendipitous smile at this simple act. Well, she did tell me to relax and enjoy myself, so I was!

Dinner was fabulous and we all raved at Darryl’s selection. It was the perfect place for a romantic dinner. I was happy that I attracted no undo attention and was just blending into the situation like any other lady. I have Linda to thank for that as she was a total knockout in her skimpy black dress that had every man’s head turning (as well as a few women’s) as we sat down.

When dinner was finished, Linda and I excused ourselves to make a necessity trip. Once inside those hallow walls of feminine sanctuary (the restroom, dummy), Linda quizzed me on how I was doing. I was only too happy to report that I was enjoying myself and that Roger had been a good choice. As we were exiting the ladies abode, she calming asked, “Then you are ready for a night of dancing?” I am sure my mouth dropped as we walked back to the table.

The men rose to assist us with our chairs. I use to think that was an insulting gesture, like a woman couldn’t pull her own seat out? But I must tell you, when you are dressed up to the nines, that little gesture makes all of the prep time seem worthwhile. Roger was rewarded with one of my best 100 watt smiles in return.

“Let’s enjoy an after dinner drink before we head to our next destination,” Darryl said. He then informed us that we would be welcoming in the New Year at a place called Valentine’s Bar.

Roger laughed at that and replied, “Darryl, what a great idea. That is the perfect place to go tonight. It will be jumping.”

Linda and I just looked at each other, not knowing what was going on. “Just wait. You will see,” Darryl replied to our unasked questions.

Valentine’s, it turns out, is one of the best gay bars in Tampa, known for their outstanding drag shows. And it was a jumping place. Somehow Darryl had gotten a table reserved for us right next to the dance floor, which allowed us easy access to dancing as well as front row seats during the drag entertainment acts. If you have never been to a drag show, you should go. The ‘girls’ were beautiful and very talented. And their gowns were to die for! It was a fun place to celebrate New Year’s Eve as everyone was there to have a good time. We danced, a lot! There was one period of time that I swear I didn’t sit down for thirty minutes as Roger insisted that we dance one song after another. I had a great time, to the point that I totally forgot about Darryl and Linda, as Roger turned out to be as smooth on the dance floor as he was off. I quickly got use to holding his hand and being in his arms during the slow songs. When midnight struck it felt quite natural to press against him and lift my face to his for our New Year kiss. Even his invading tongue was welcomed by that time. When we broke I realized that Linda had made sure that she was close by to watch it happen. She stepped up and we shared a kiss as well as she turned out to be the second person to kiss me in 2009. Darryl took her place when we finished and I accepted his kiss easily. What a way to start the New Year.

We stayed and danced and drank Champagne for another hour, then headed back to the condo. Roger, realizing my resistance was low, enjoyed more kisses on the drive as we made out like teenagers in the back seat. Linda had to say something to us to let us know that we had arrived as we were in our own little world.

Back inside the condo, we all decide that we had had enough to drink so cocktails were passed on. The awkwardness of the situation started to surface when Linda announced that she was going to retire for the night and pulled Darryl towards the bedroom. I wasn’t sure what to do next, but as I heard their door close Roger pulled me into his arms and kissed me. We stood kissing for a long time, then I felt the hand on my back reach up for the dress’ zipper, followed by the sound and pull of the zipper traveling down. As our kissing continued I felt the cold air on my back as the dress pulled open. I wasn’t sure what to do, but felt Roger’s hands on my shoulders as he pushed the dress off of them. Almost without thinking, I slipped my arms out of the sleeves and felt the dress puddle around my high heels. Still not breaking the kiss, I stepped out of the dress with one foot and kicked the dress away with the other. Where had I learned that maneuver? So there I was, standing in my underwear, kissing my date in the living room of his condo. I never saw that coming!

When the kiss broke, Roger took my hand and silently led me to my bedroom (well, technically his bedroom, or his guest room… oh, just forget it). I turned the light on the nightstand on, then was pulled onto the bed where the kissing resumed. Now how did I get into this predicament? And how was I going to get out of it? Two good questions that were about to be resolved.

As we kissed, Roger cupped by breast and my hand traveled down to cup his cock. We each started slowing massaging our prizes. With a mind of its own, at least that’s what I am telling myself, my hand unbuckled his belt and unzipped the pants. He lifted his hips in assistance as I tugged at the pants, pulling them down past him knees. That nasty hand of mine wasn’t satisfied rubbing his cock through his underwear for long, and the Jockeys quickly joined the pants.

For the second time in less then twelve hours, I found myself with another man’s cock in my hand. And, for the second time in less then twelve hours, my mouth soon found its way down to my hand and I tasted my second cock. I must have been doing a good job because Roger was speechless and reduced to animal sounds. It wasn’t long before I knew that I was doing a good job as I was rewarded for my efforts. I thought that the evening would come to an end then. However, Roger, being the gentleman that he is, returned the favor to me. Fifteen minutes later I was asleep in his arms.

And thus began 2009! But wait, there’s more!